Imidazole → HCID 123462581, compound

HRID 1508652Notes

Reaction equation

HRID 1508652 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[OH:12][CH2:13][C@@H:14]1[O:18][C:17]([CH3:20])([CH3:19])[O:16][C@@H:15]1[C@H:21]([OH:23])[CH3:22].N1C=CN=C1.C(OCC)(=O)C>CN(C)C=O.O>[CH3:20][C:17]1([CH3:19])[O:16][C@H:15]([C@H:21]([OH:23])[CH3:22])[C@H:14]([CH2:13][O:12][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2])[O:18]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 139400Triisopropylsilyl chlorideHCID 14037645HCID 14037645, compound

Product 1

HCID 123462581HCID 123462581, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4.46 mL of triisopropylsilyl chloride was added dropwise to a solution of 3.5 g of (1R)-1-((4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-yl)ethan-1-ol and 1.63 g of imidazole in 50 mL of N,N-dimethylformamide in a nitrogen atmosphere at a temperature of 5° C. to 10° C., and the obtained mixture was then stirred at room temperature for 23 hours. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated, and it was washed with a saturated sodium chloride aqueous solution and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, so as to obtain 7.1 g of (1R)-1-((4R,5S)-2,2-dimethyl-5-(((tris(propan-2-yl)silyl)oxy)methyl)-1,3-dioxolane-4-yl)ethan-1-ol in the form of a colorless oily product.

Workup

  1. washit was washed with a saturated sodium chloride aqueous solution
  2. dry with materialwas then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-af267cfb50e94b33a1afc39e0435b544
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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